#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/19/2241990.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241990
loop_
_publ_author_name
'Hernández, Yaiza'
'Marcos, Isidro'
'Garrido, Narciso M.'
'Sanz, Francisca'
'Diez, David'
_publ_section_title
;
 Crystal structure of
 (2R*,3aR*)-2-phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole
;
_journal_coeditor_code           RZ5200
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              85
_journal_page_last               87
_journal_paper_doi               10.1107/S2056989016019952
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C12 H15 N O3 S'
_chemical_formula_moiety         'C12 H15 N O3 S'
_chemical_formula_sum            'C12 H15 N O3 S'
_chemical_formula_weight         253.31
_chemical_name_systematic
(2R*,3aR*)-2-Phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.754(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5730(4)
_cell_length_b                   5.4443(2)
_cell_length_c                   18.2266(6)
_cell_measurement_reflns_used    1548
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.1
_cell_measurement_theta_min      8.7
_cell_volume                     1236.22(7)
_computing_cell_refinement
;
SAINT (Bruker 2006)
;
_computing_data_collection
;
APEX2 (Bruker 2006)
;
_computing_data_reduction
;
SAINT (Bruker 2006)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
SHELXTL/PC (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9571
_diffrn_reflns_theta_full        66.77
_diffrn_reflns_theta_max         66.77
_diffrn_reflns_theta_min         8.50
_exptl_absorpt_coefficient_mu    2.311
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2006)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.5869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                1949
_reflns_number_total             2074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz5200sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2241990
_cod_database_fobs_code          2241990
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.18509(4) 0.20282(9) 0.19580(3) 0.0506(2) Uani d . 1 1
O O1 0.27595(12) 0.0779(4) 0.33002(8) 0.0780(5) Uani d . 1 1
O O2 0.10289(12) 0.0979(4) 0.14263(9) 0.0745(5) Uani d . 1 1
O O3 0.17911(13) 0.4582(3) 0.21257(10) 0.0722(5) Uani d . 1 1
N N1 0.24857(16) 0.2358(4) 0.38806(12) 0.0767(6) Uani d . 1 1
C C1 0.2723(3) 0.0922(13) 0.45671(19) 0.173(3) Uani d . 1 1
H H1A 0.3095 -0.0579 0.4469 0.207 Uiso calc R 1 1
H H1B 0.3185 0.1863 0.4933 0.207 Uiso calc R 1 1
C C2 0.1731(3) 0.0332(7) 0.48481(17) 0.1044(11) Uani d . 1 1
H H2A 0.1821 0.0422 0.5384 0.125 Uiso calc R 1 1
H H2B 0.1487 -0.1303 0.4696 0.125 Uiso calc R 1 1
C C3 0.0964(3) 0.2227(6) 0.45154(17) 0.0932(9) Uani d . 1 1
H H3A 0.1018 0.3717 0.4810 0.112 Uiso calc R 1 1
H H3B 0.0231 0.1629 0.4466 0.112 Uiso calc R 1 1
C C4 0.13178(19) 0.2665(5) 0.37671(14) 0.0653(6) Uani d . 1 1
H H4 0.1134 0.4343 0.3602 0.078 Uiso calc R 1 1
C C5 0.08854(17) 0.0856(5) 0.31715(13) 0.0669(6) Uani d . 1 1
H H5A 0.0605 -0.0600 0.3385 0.080 Uiso calc R 1 1
H H5B 0.0322 0.1592 0.2824 0.080 Uiso calc R 1 1
C C6 0.18549(16) 0.0244(4) 0.27984(11) 0.0548(5) Uani d . 1 1
H H6 0.1848 -0.1510 0.2677 0.066 Uiso calc R 1 1
C C7 0.31162(15) 0.1448(4) 0.16793(11) 0.0489(5) Uani d . 1 1
C C8 0.3261(2) -0.0590(5) 0.12636(15) 0.0748(7) Uani d . 1 1
H H8 0.2699 -0.1680 0.1129 0.090 Uiso calc R 1 1
C C9 0.4260(3) -0.0996(6) 0.10473(19) 0.0949(9) Uani d . 1 1
H H9 0.4371 -0.2375 0.0766 0.114 Uiso calc R 1 1
C C10 0.5086(2) 0.0610(7) 0.12436(18) 0.0902(9) Uani d . 1 1
H H10 0.5754 0.0320 0.1095 0.108 Uiso calc R 1 1
C C11 0.4932(2) 0.2622(6) 0.16530(18) 0.0843(8) Uani d . 1 1
H H11 0.5495 0.3712 0.1783 0.101 Uiso calc R 1 1
C C12 0.39431(18) 0.3066(4) 0.18785(14) 0.0650(6) Uani d . 1 1
H H12 0.3839 0.4444 0.2162 0.078 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O2 118.54(11)
O3 S1 C7 108.17(9)
O2 S1 C7 109.24(10)
O3 S1 C6 109.58(10)
O2 S1 C6 106.06(10)
C7 S1 C6 104.34(9)
C6 O1 N1 110.65(15)
O1 N1 C4 107.39(17)
O1 N1 C1 105.4(3)
C4 N1 C1 105.4(2)
C2 C1 N1 109.5(3)
C2 C1 H1A 109.8
N1 C1 H1A 109.8
C2 C1 H1B 109.8
N1 C1 H1B 109.8
H1A C1 H1B 108.2
C1 C2 C3 104.2(3)
C1 C2 H2A 110.9
C3 C2 H2A 110.9
C1 C2 H2B 110.9
C3 C2 H2B 110.9
H2A C2 H2B 108.9
C2 C3 C4 103.0(2)
C2 C3 H3A 111.2
C4 C3 H3A 111.2
C2 C3 H3B 111.2
C4 C3 H3B 111.2
H3A C3 H3B 109.1
N1 C4 C3 105.5(2)
N1 C4 C5 106.48(18)
C3 C4 C5 115.1(2)
N1 C4 H4 109.8
C3 C4 H4 109.8
C5 C4 H4 109.8
C6 C5 C4 103.48(17)
C6 C5 H5A 111.1
C4 C5 H5A 111.1
C6 C5 H5B 111.1
C4 C5 H5B 111.1
H5A C5 H5B 109.0
O1 C6 C5 107.19(17)
O1 C6 S1 110.63(15)
C5 C6 S1 110.59(15)
O1 C6 H6 109.5
C5 C6 H6 109.5
S1 C6 H6 109.5
C8 C7 C12 120.9(2)
C8 C7 S1 119.84(17)
C12 C7 S1 119.31(16)
C7 C8 C9 118.8(3)
C7 C8 H8 120.6
C9 C8 H8 120.6
C10 C9 C8 120.6(3)
C10 C9 H9 119.7
C8 C9 H9 119.7
C11 C10 C9 120.1(2)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 120.4(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C7 C12 C11 119.2(2)
C7 C12 H12 120.4
C11 C12 H12 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4277(16)
S1 O2 1.4364(16)
S1 C7 1.763(2)
S1 C6 1.813(2)
O1 C6 1.391(3)
O1 N1 1.440(3)
N1 C4 1.465(3)
N1 C1 1.472(5)
C1 C2 1.446(5)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.485(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.510(4)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.511(4)
C4 H4 0.9800
C5 C6 1.511(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6 0.9800
C7 C8 1.370(3)
C7 C12 1.374(3)
C8 C9 1.384(4)
C8 H8 0.9300
C9 C10 1.367(5)
C9 H9 0.9300
C10 C11 1.354(5)
C10 H10 0.9300
C11 C12 1.382(4)
C11 H11 0.9300
C12 H12 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 O3 1_545 0.98 2.35 3.314(3) 167.8
C11 H11 O1 2_655 0.93 2.49 3.364(3) 157.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101568039
